2,6-dimethylquinoline-4-carboxylic acid → HCID 86714309, compound

HRID 1483987Notes

Reaction equation

HRID 1483987 reaction equation
Cl.[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][NH2+:18]3)=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:10])(=[O:9])[N:8]=1.[CH3:23][C:24]1[CH:33]=[C:32]([C:34](O)=[O:35])[C:31]2[C:26](=[CH:27][CH:28]=[C:29]([CH3:37])[CH:30]=2)[N:25]=1>>[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3[C:34]([C:32]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([CH3:37])[CH:30]=4)[N:25]=[C:24]([CH3:23])[CH:33]=3)=[O:35])=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:9])(=[O:10])[N:8]=1

Participants

3

Reactant 2

HCID 7877222,6-dimethylquinoline-4-carboxylic acidHCID 86714283(R)-2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochloride

Product 1

HCID 86714309HCID 86714309, compound

Procedure

Prepared as in Example 15 from (R)-2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)piperidinium hydrochloride (Example 15a) and 2,6-dimethylquinoline-4-carboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ 1.12-1.53 (m, 2H), 1.58-1.84 (m, 4H), 1.98 (s, 3H), 2.64 (s, 3H), 3.02 (m, 1H), 3.19 (m, 1H), 4.18 (dd, 1H, J=9.9, 3.1 Hz), 4.95 (t, 1H, J=10.2 Hz), 5.45 (m, 1H), 6.66 (m, 1H), 7.01 (d, 1H, J=8.2 Hz), 7.27 (s, 1H), 7.38 (s, 1H), 7.46-7.61 (m, 2H), 7.81 (d, 1H, J=8.6 Hz), 7.98 (br s, 1H), 8.26 (br s, 1H), 10.94 (s, 1H). MS 494 (MH+).

Sources & evidence

ORD record
ord-e7b1bbc1095b4051ab0801596174bee1
Source dataset
uspto-grants-2016_08
Patent number
US09420814B2

Reaction notes

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